Patent GB-1034957-A (GB)
Title: Bromoethyl-thioethers and their use in acaricidal compositions
IPC: F04B1/08
Filed: 1964-08-04
Abstract: The invention relates to compounds of the general formula R-S-CH2-CH2-Br in which R is (a) a phenyl radical mono-substituted in one of the positions ortho or meta by a halogen atom or an alkyl group of from 1 to 4 carbon atoms, or mono-substituted in any position by the formyl group or by an alkoxy group of from 1 to 4 carbon atoms or an alkoxy-carbonyl group of from 2 to 5 carbon atoms, (b) a phenyl radical di-substituted by halogen, alkyl of from 1 to 4 carbon atoms, the two substituents being same or different, (c) an unsubstituted alpha- or beta-naphthyl radical, (d) a mono - substituted alpha- and beta-naphthyl radical substituted with one of the following substituents: halogen, formyl, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, alkoxy-carbonyl of from 2 to 5 carbon atoms, or (e) a di-substituted alpha- and beta-naphthyl radical substituted with two of the following substituents: halogen, lower alkyl, lower alkoxy, these substituents being same or different.  Compounds claimed per se are S - b  - bromoethyl - S - 2 - methoxyphenyl - sulfide, S - b  - bromoethyl - S - 3 - chloro - phenyl - sulfide, S - b  - bromoethyl - S-3 - methyl - phenyl - sulfide, S - b  - bromoethyl-S - 3 - methoxy - phenyl - sulfide, S - b  - bromoethyl - S - I - naphthyl - sulfide, S - b  - bromoethyl - S - 2 - naphthyl sulfide, S - b  - bromoethyl - S - 2 - chlorophenyl - sulfide, - S - b - bromoethyl - S - 2 - methyl - phenyl - sulfide. The compounds may be prepared by reacting a correspondingly substituted thiophenol or thionaphthol with (a) 1,2-ethylene halogenohydrin in the presence of an acid acceptor, and an inert solvent and treating the product obtained with a brominating agent; (b) with ethylene oxide and treating the product obtained with a brominating agent; (c) with an excess of 1,2-diobromoethane. In an example S-b -bromoethyl-S-m-tolyl-sulfide The latter is obtained by reacting phosphorus tribromide with b -(m-tolylthio)-ethanol. The latter is obtained by reacting m-thiocresol and ethylene chlorohydrin.ALSO:Acaricidal compositions comprising active ingredient a b -bromoethyl-aryl-thiother of the formula R-S-CH2-CH2-Br wherein R represents:  a) a phenyl radical mono-substituted in one of the positions ortho or meta by an halogen atom or an alkyl group of from 1 to 4 carbon atoms, or monosubstituted in any position by the formyl or nitro group or by an alkoxy group of from 1 to 4 carbon atoms or an alkoxy-carbonyl group of from 2 to 5 carbon atoms,  (b) a phenyl radical disubstituted by halogen, alkyl of from 1 to 4 carbon atoms or alkoxy of from 1 to 4 carbon atoms, the two substituents being same or different,  (c) an unsubstituted alpha-and beta-radical  (d) a mono-substituted alpha- and beta-naphthyl radical substituted with one of the following substituents: halogen, formyl, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, alkoxy-carbonyl of from 2 to 5 carbon atoms, or  (e) a disubstituted alpha- and beta-naphthyl radical substituted with two of the following substituents: halogen, lower alkyl, lower alkoxy, these substituents being same or different.  together with a non-phytotosic carrier therefor. Specified active ingredients are:-  S-b -bromoethyl-S-2-methoxy-phenyl-sulfide, S-b -bromoethyl-S-3-chloro-phenyl-sulfide, S-b -bromoethyl-S-3-methyl-phenyl-sulfide, S-b -bromoethyl-S-3-methoxy-phenyl-sulfide, S-b -bromoethyl-S-1-naphthyl-sulfide, S-b -bromoethyl-S-2-naphthyl-sulfide, S-b -bromoethyl-S-2-chlorophenyl-sulfide, S-b -bromoethyl-S-2-methyl-phenyl-sulfide.